Morpholine → 4-[[2-Bromo-5-(trifluoromethyl)phenyl]methyl]morpholine

HRID 1524064Notes

Reaction equation

HRID 1524064 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:7]([C:10]([F:13])([F:12])[F:11])=[CH:6][C:3]=1[CH:4]=O.[NH:14]1[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1.[BH4-].[Na+]>C(Cl)Cl>[Br:1][C:2]1[CH:9]=[CH:8][C:7]([C:10]([F:13])([F:12])[F:11])=[CH:6][C:3]=1[CH2:4][N:14]1[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1

Participants

5

Reactant 3

HCID 8083MorpholineHCID 4311764Sodium borohydrideHCID 70180472-Bromo-5-(trifluoromethyl)benzaldehyde

Product 1

HCID 748919354-[[2-Bromo-5-(trifluoromethyl)phenyl]methyl]morpholine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Bromo-5-(trifluoromethyl)benzaldehyde (266 mg, 1.05 mmol) and morpholine (0.10 mL, 1.2 mmol) were dissolved in DCM (2 mL), stirred for 20 minutes, and then treated with NaBH4 (79 mg, 2.1 mmol). The reaction was stirred overnight at rt, after which time, the reaction was quenched by the slow addition of water (10 mL). The aqueous layer was further extracted with DCM (3×10 mL), dried over sodium sulfate, filtered, and concentrated to dryness. The crude product was purified by FCC to provide the title compound. 1H NMR (500 MHz, CDCl3) δ 7.77 (s, 1H), 7.67 (d, J=8.3, 1H), 7.37 (d, J=8.3, 1H), 3.80-3.69 (m, 4H), 3.63 (d, J=1.7, 2H), 2.59-2.49 (m, 4H).

Workup

  1. stirringThe reaction was stirred overnight at rt
  2. customafter which time, the reaction was quenched by the slow addition of water (10 mL)
  3. extractionThe aqueous layer was further extracted with DCM (3×10 mL)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated to dryness
  7. customThe crude product was purified by FCC

Sources & evidence

ORD record
ord-c14ad725c36548b1addb1c6943ead424
Source dataset
uspto-grants-2015_07
Patent number
US09079866B2

Reaction notes

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